Holiday homes by the sea in Islamorada

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B&B and Vacation Rentals
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FACILITIES

  • Pool
  • Pets Allowed
  • Non Smoking Only

REVIEWS

  • 9+ Exceptional
  • 8+ Fabulous
  • 7+ Very Good

DISTANCE FROM CENTRE

  • Less than 1 km
  • Less than 3 km
  • Less than 5 km

Holiday rental deals in Islamorada

We have selected the best holiday accommodation by the sea in Islamorada. Bluepillow allows you to save money, by finding the best rates on the main vacation rental websites in Islamorada

  • Luxury One Bedroom Condo #4

    • 2 Guests · 1Bedroom
    9.6 Exceptional (4)
    Located in Islamorada, this condo is by the sea. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater Archaeological ...
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  • Hidden Gem Islamorada Top Floor 2Bed/2Bath

    • 4 Guests · 2Bedrooms
    9.9 Exceptional (31)
    Located in Islamorada, this apartment is by the sea. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian ...
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  • Hidden Gem Islamorada 1st Floor 2Bed/2Bath

    • 4 Guests · 2Bedrooms
    9.7 Exceptional (33)
    Located in Islamorada, this apartment is on the waterfront. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, ...
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  • Islamorada Condo with ocean access

    • 4 Guests · 2Bedrooms
    9.6 Exceptional (10)
    Located in Islamorada, this condo is on the waterfront. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore ...
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  • Oceanfront Islamorada Condo with T-Dock FREE boat dockage

    • 4 Guests · 2Bedrooms
    9.6 Exceptional (19)
    Located in Islamorada, this condo is on the beach. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
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  • Ocean & Bay Views. Welcome To Paradise!

    • 2 Guests · 1Bedroom
    9.8 Exceptional (27)
    Located in Islamorada, Ocean & Bay Views. Welcome To Paradise! is on the waterfront. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while ...
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  • Luxury One Bedroom Condo #3

    • 2 Guests · 1Bedroom
    10 Exceptional (5)
    This condo is located in Islamorada. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve ...
    Check Availability

  • Luxury One Bedroom Condo #2

    • 2 Guests · 1Bedroom
    10 Exceptional (4)
    This condo is located in Islamorada. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, those looking for an ...
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  • Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

    • 6 Guests · 3Bedrooms
    9.8 Exceptional (47)
    Located in Islamorada, this condo is in the city center and on the beach. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural ...
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  • New Modern Penthouse with Private Beach

    • 8 Guests · 4Bedrooms
    9.8 Exceptional (8)
    Located in Islamorada, this condo is on the beach. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
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  • Oceanfront condo REMODELED 3/2 pool steps from balcony MM80 on ocean!

    • 6 Guests · 3Bedrooms
    9.8 Exceptional (27)
    Located in Islamorada, this condo is on the beach. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
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  • 3 bedroom, 3.5 bath luxurious condo 402 at Maison in Islamorada

    • 6 Guests · 3Bedrooms
    This condo is located in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural ...
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  • Beautiful Ocean Front 2 Story Townhouse

    • 6 Guests · 2Bedrooms
    Located in Islamorada, this condo is on the waterfront. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater ...
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  • 3 bedroom ocean front, pool front boutique Condo in Islamorada, Florida Keys

    • 8 Guests · 3Bedrooms
    10 Exceptional (4)
    This condo is located in Islamorada. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, those looking for an ...
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  • 4 BR Ocean front Condo in Islamorada, FL Keys steps away from pool & sandy beach

    • 8 Guests · 4Bedrooms
    This condo is located in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural ...
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  • 1 Bedroom apartment in the HEART of Islamorada, Upper Matecumbe Key

    • 2 Guests · 1Bedroom
    This apartment is located in Islamorada. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian Key Historic ...
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  • Luxury One Bedroom Condo #4

    • 2 Guests · 1Bedroom
    9.4 Exceptional (3)
    Located in Islamorada, this condo is by the sea. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater Archaeological ...
    Check Availability

  • The Oasis

    • 8 Guests · 3Bedrooms
    Boasting air-conditioned accommodation with a private pool, lake view and a patio, The Oasis is situated in Islamorada. Set on the beachfront, this property has an outdoor swimming pool, a garden and a ...
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  • Anglers Reef Paradise

    • 6 Guests · 2Bedrooms
    Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi. ...
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  • Islamorada Bungalows Suite 4

    • 2 Guests · 1Bedroom
    7.5 Very Good (4)
    Located in Islamorada, this apartment is in the city center. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater ...
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Bed and breakfast offers in Islamorada by the sea

Are you looking for an accommodation in Islamorada and do you want to save money? Choose from 2 Bed & Breakfasts in Islamorada

  • Anglers Reef Villa 1

    • Hotel
    9.4 Exceptional (9)
    Located in Islamorada, Anglers Reef Villa 1 is within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Islamorada County Park. This beach villa is 1.8 mi (2.9 km) from Founders Park ...
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  • The Islands of Islamorada

    • Hotel
    9.6 Exceptional (57)
    When you stay at The Islands of Islamorada in Islamorada, you'll be on the beach, within a 5-minute drive of History of Diving Museum and Matecumbe United Methodist Church. This 4-star villa is 1.4 mi ...
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Farmhouse or Hotel? Choose from the best offers

Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?

  • Farmstays in Islamorada
    Farmstays in Islamorada
  • Hotels in Islamorada
    Hotels in Islamorada

Hotels in Islamorada, our top selection just for you

Are you looking for hotels in Islamorada? Here is a selection of the best hotels in Islamorada

  • The Caribbean Resort

    • Hotel
    9.8 Exceptional (375)
    A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud ...
    Check Availability

  • Pines & Palms Resort

    • Hotel
    9 Exceptional (3013)
    Located in Islamorada, Pines & Palms Resort is on a private beach. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed ...
    Check Availability

  • Casa Morada

    • Hotel
    9.3 Exceptional (837)
    Located in Islamorada, Casa Morada is near the beach. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore ...
    Check Availability

  • La Jolla Resort

    • Hotel
    8.7 Fabulous (2296)
    Ideally located in the Upper Matecumbe Key area, La Jolla Resort Islamorada promises a relaxing and wonderful visit. The property offers a high standard of service and amenities to suit the individual ...
    Check Availability

  • Chesapeake Beach Resort

    • Hotel
    8 Fabulous (2139)
    Located in Upper Matecumbe Key, Chesapeake Beach Resort is a perfect starting point from which to explore Islamorada (FL). Offering a variety of facilities and services, the property provides all you need ...
    Check Availability

  • Amara Cay Resort

    • Hotel
    6.3 Pleasant (3722)
    Located in Upper Matecumbe Key, Amara Cay Resort is a perfect starting point from which to explore Islamorada (FL). Featuring a satisfying list of amenities, guests will find their stay at the property ...
    Check Availability

  • Sands of Islamorada

    • Hotel
    8.6 Fabulous (855)
    This Islamorada, Florida inn boasts an outdoor pool with a hot tub and a boat dock with a ramp. Guests will be 4 miles from Theater of the Sea and 2 miles of Indian Key Historic State Park. ...
    Check Availability

  • Islander Bayside Villas & Boatslips

    • Hotel
    8.9 Fabulous (780)
    Located on the waters of the Florida Bay, the Islander Bayside Resort is less than 5 minutes’ walk from the beach. This resort features a kitchen in every townhouse and an outdoor pool. ...
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  • Islander Resort

    • Hotel
    9.1 Exceptional (3665)
    A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. ...
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  • Fisher Inn Resort & Marina

    • Hotel
    7.3 Very Good (2176)
    Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games ...
    Check Availability

  • Postcard Inn Beach Resort & Marina

    • Hotel
    8.3 Fabulous (2829)
    Stop at Postcard Inn Beach Resort & Marina at Holiday Isle to discover the wonders of Islamorada (FL). The hotel offers a high standard of service and amenities to suit the individual needs of all travelers. ...
    Check Availability

  • Cheeca Lodge & Spa

    • Hotel
    8.7 Fabulous (2550)
    Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot ...
    Check Availability

  • Hadley House Islamorada

    • Hotel
    7.8 Very Good (1725)
    This beachfront hotel is located in Islamorada, Florida. Hadley House Islamorada features an outdoor swiming pool and free WiFi throughout the property. ...
    Check Availability

  • Breezy Palms Resort

    • Hotel
    8.2 Fabulous (322)
    Located in Islamorada, Breezy Palms Resort is on the beach. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, ...
    Check Availability

  • Oceanfront Home w/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center

    • Hotel
    10 Exceptional (2)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Large Caribbean-Style Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda

    • Hotel
    10 Exceptional (2)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Spacious Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda

    • Hotel
    10 Exceptional (1)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool

    • Hotel
    10 Exceptional (5)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Spacious Caribbean-Style Home w/ Kitchen, WiFi, Grill, & Outdoor Veranda

    • Hotel
    10 Exceptional (1)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability
Discover all the offers >

The best hotels with swimming pool in Islamorada

Book your relaxing holiday, by choosing the best deals at hotels with swimming pools in Islamorada

  • The Caribbean Resort

    • Hotel
    9.8 Exceptional (375)
    A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud ...
    Check Availability

  • Pines & Palms Resort

    • Hotel
    9 Exceptional (3013)
    Located in Islamorada, Pines & Palms Resort is on a private beach. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed ...
    Check Availability

  • Casa Morada

    • Hotel
    9.3 Exceptional (837)
    Located in Islamorada, Casa Morada is near the beach. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore ...
    Check Availability

  • La Jolla Resort

    • Hotel
    8.7 Fabulous (2296)
    Ideally located in the Upper Matecumbe Key area, La Jolla Resort Islamorada promises a relaxing and wonderful visit. The property offers a high standard of service and amenities to suit the individual ...
    Check Availability

  • Chesapeake Beach Resort

    • Hotel
    8 Fabulous (2139)
    Located in Upper Matecumbe Key, Chesapeake Beach Resort is a perfect starting point from which to explore Islamorada (FL). Offering a variety of facilities and services, the property provides all you need ...
    Check Availability

  • Amara Cay Resort

    • Hotel
    6.3 Pleasant (3722)
    Located in Upper Matecumbe Key, Amara Cay Resort is a perfect starting point from which to explore Islamorada (FL). Featuring a satisfying list of amenities, guests will find their stay at the property ...
    Check Availability

  • Sands of Islamorada

    • Hotel
    8.6 Fabulous (855)
    This Islamorada, Florida inn boasts an outdoor pool with a hot tub and a boat dock with a ramp. Guests will be 4 miles from Theater of the Sea and 2 miles of Indian Key Historic State Park. ...
    Check Availability

  • Islander Bayside Villas & Boatslips

    • Hotel
    8.9 Fabulous (780)
    Located on the waters of the Florida Bay, the Islander Bayside Resort is less than 5 minutes’ walk from the beach. This resort features a kitchen in every townhouse and an outdoor pool. ...
    Check Availability

  • Islander Resort

    • Hotel
    9.1 Exceptional (3665)
    A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. ...
    Check Availability

  • Fisher Inn Resort & Marina

    • Hotel
    7.3 Very Good (2176)
    Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games ...
    Check Availability

  • Postcard Inn Beach Resort & Marina

    • Hotel
    8.3 Fabulous (2829)
    Stop at Postcard Inn Beach Resort & Marina at Holiday Isle to discover the wonders of Islamorada (FL). The hotel offers a high standard of service and amenities to suit the individual needs of all travelers. ...
    Check Availability

  • Cheeca Lodge & Spa

    • Hotel
    8.7 Fabulous (2550)
    Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot ...
    Check Availability

  • Hadley House Islamorada

    • Hotel
    7.8 Very Good (1725)
    This beachfront hotel is located in Islamorada, Florida. Hadley House Islamorada features an outdoor swiming pool and free WiFi throughout the property. ...
    Check Availability

  • Breezy Palms Resort

    • Hotel
    8.2 Fabulous (322)
    Located in Islamorada, Breezy Palms Resort is on the beach. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, ...
    Check Availability

  • Oceanfront Home w/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center

    • Hotel
    10 Exceptional (2)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Large Caribbean-Style Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda

    • Hotel
    10 Exceptional (2)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Spacious Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda

    • Hotel
    10 Exceptional (1)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool

    • Hotel
    10 Exceptional (5)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability

  • Spacious Caribbean-Style Home w/ Kitchen, WiFi, Grill, & Outdoor Veranda

    • Hotel
    10 Exceptional (1)
    Located in Islamorada, this resort is by the sea. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
    Check Availability
Discover all the offers >

Accommodation and holiday homes in Islamorada

In and around Islamorada the tourist has at disposal various types of holiday accommodation for holidays by the sea, for a lone traveller, a small or large family or even a group.
Islamorada offers: 195 apartments, 33 hotels, 2 b&bs, 199 independent homes, 40 villas and much more by the sea.
The accommodation in this area has positive reviews: the tourists have written 654 reviews with a score of 10.0 Excellent and 63 reviews with a score of 8.0 Very Good, over a total of 23,139 reviews.
For your stay in the enchanting destination Islamorada, the best features are Pool, Pets Allowed, Non Smoking Only, Kitchen and Spa.

Islamorada: the best offers for the best accommodation and holiday homes

How much doeas it cost to stay in Islamorada? The more economical accommodation in Islamorada has an average cost of 741 pounds per night.

What to do in Islamorada

In Islamorada, the best accommodation near the sea can also be found near the major interest points.

Only a few km from the sea you can find 277 accommodation options available at the best price: 195 Apartments, 2 B&Bs, 33 Hotels, and much more. Below you can find the best apartments near the beaches.
A Islamorada, furthermore, much of the best accommodation is close to the best beaches in the area: 17 Apartments, B&Bs, Hotels, and much more.

The weather forcast in Islamorada

Islamorada: during the year, the average temperature throughout the year is around 26°C. The coldest period of the year is in the month of January where the temperature can drop to 22°C. The hottest month of the year is instead in July where the maximum temperature can reach 29°C.

Top Regions in Islamorada

Windley Key

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